Technical Services Manager – CMMC Service Delivery; Red Cup Powered by Treeline

Company: Red Cup

Department: Technical Services / Service Delivery

Reports To: Director of Operations

Position Type: Full-Time

Location: Remote, U.S.-Based

Interview Requirements: In-Person for Final Round

Position Summary

Red Cup is a managed services provider (MSP) and part of Treeline, a technology services organization spanning managed IT, cybersecurity, compliance, and advisory services. As Treeline expands its compliance business, Red Cup is building a dedicated Technical Services pod to support clients with CMMC and other regulated technology requirements. The pod will be staffed and managed by Red Cup, operate within its established service delivery model, and be dedicated to Treeline’s compliance business and clients.

The Technical Services Manager (TSM) will lead this pod, combining hands-on technical expertise, team leadership, and service delivery ownership with disciplined execution of security and compliance requirements. The TSM is accountable for high-quality technical support while ensuring adherence to required processes, access controls, security standards, and documentation.

The ideal candidate brings strong MSP experience, broad expertise across cloud, identity, endpoint, and security platforms, and experience leading technical teams supporting regulated environments.

Key Responsibilities

Pod Leadership & Service Delivery

• Lead the day-to-day performance and operations of a dedicated technical services pod.

• Manage, coach, and develop L1, L2, and L3 technical resources.

• Own pod performance across ticket response, resolution, SLA attainment, quality, client experience,

and technical escalation management.

• Monitor workload, capacity, ticket aging, escalations, and service trends and proactively address risks.

• Serve as the senior technical escalation point for complex or high-impact client issues.

• Maintain strong operational discipline around documentation, ticket quality, change management, and escalation procedures.

• Partner with Client Success, Service Coordination, Engineering, Projects, Security, and Compliance teams to ensure seamless client delivery.

• Identify opportunities to improve service quality, efficiency, and scalability across the pod.

CMMC Regulated Environment Support

• Lead technical service delivery for clients subject to CMMC and related NIST SP 800-171 security requirements.

• Ensure technicians understand and consistently follow client-specific security policies, procedures, access requirements, and approved workflows.

• Reinforce proper handling of Controlled Unclassified Information (CUI) and other sensitive information within approved systems and environments.

• Ensure administrative access, privileged activities, remote support, and technical changes follow established security controls and authorization processes.

• Maintain documentation and ticketing practices capable of supporting compliance evidence and assessment requirements.

• Partner with Security and Compliance stakeholders to remediate technical findings, control gaps, vulnerabilities, and corrective actions.

• Support evidence collection and technical validation activities associated with CMMC readiness and assessments.

• Identify service delivery practices that could introduce compliance or security risk and ensure they areappropriately addressed or escalated.

The TSM is not expected to independently serve as the organization's CMMC assessor or compliance officer. The role is responsible for ensuring the technical services organization executes consistently within the established compliance framework.

Technical Leadership

• Provide technical leadership across Microsoft 365 and Google Workspace environments, identity and access management platforms including Entra ID and Okta, endpoint management platforms including Intune and other MDM/RMM solutions, Windows and macOS environments, networking, endpoint security, and cloud infrastructure.

• Troubleshoot and lead resolution of complex technical issues across endpoint, identity, cloud, networking, and security environments.

• Ensure identity, access, device, and security configurations align with established client security standards and documented compliance requirements.

• Provide leadership around MFA, SSO, conditional access, role-based access, least privilege, privileged access, and secure administrative practices.

• Partner with Engineering and Security teams on technical standards, automation, hardening, and continuous improvement initiatives.

• Drive root cause analysis for recurring or significant technical incidents.

• Identify opportunities to reduce ticket volume and improve reliability through automation, standardization, and proactive remediation.

• Ensure technical changes are appropriately documented, tested, approved, and executed.

Required Qualifications

• 5+ years of experience in IT service delivery, managed services, systems administration, or technical support.

• 2+ years of experience leading technical teams in an MSP or similarly fast-paced service environment.

• Strong technical experience across Microsoft 365 and/or Google Workspace environments.

• Hands-on experience with identity and access management platforms (ex: Entra ID, Okta).

• Experience with endpoint management platforms such as Intune and other MDM/RMM solutions across Windows and macOS environments.

• Working knowledge of networking, endpoint security, EDR/MDR, vulnerability management, secure remote access, and cloud security technologies.

• Experience supporting organizations operating under CMMC, NIST SP 800-171, DFARS, or comparable regulated security frameworks.

• Strong understanding of least privilege, MFA, privileged access, endpoint security, vulnerability management, change control, and secure remote administration.

• Demonstrated ability to lead technical escalations and communicate effectively with both technical and non-technical stakeholders.

• Strong documentation, process management, and operational discipline.

• U.S.-based and able to meet client-specific personnel, access, or data-handling requirements associated with regulated environments.

Preferred Qualifications

• Experience supporting Department of Defense contractors or organizations handling CUI.

• Direct experience supporting CMMC Level 2 environments.

• Familiarity with Microsoft GCC/GCC High and/or Google Workspace environments used by regulated organizations.

• Experience with Entra ID, Okta, Intune, and other enterprise identity and endpoint management platforms.

• Experience preparing technical documentation or evidence for CMMC, NIST SP 800-171, or other security assessments.

• Experience with SIEM/MDR, EDR, SASE, vulnerability management, application control, and privileged access technologies.

• Microsoft, Google, Okta, security, networking, or CMMC-related certifications.

• Experience working with ConnectWise or similar PSA platforms and modern RMM tooling.

Success Measures

Success in this role will be measured by:

SLA and service delivery performance.
• Ticket quality, aging, and resolution performance.
• Client satisfaction and effective escalation management.
• Pod productivity, capacity management, and team development.
• Consistent adherence to security and compliance procedures.
• Quality and completeness of technical documentation.
• Timely remediation and escalation of identified technical and compliance risks.
• Reduction of recurring issues through root cause analysis and continuous improvement.
• Readiness of service delivery records and technical evidence to support client compliance
requirements.
• Ability to maintain strong service delivery while operating within the security controls required by
regulated client environments.

Leadership Expectations

The Technical Services Manager is expected to operate as a player-coach. This role requires someone who can lead the team, develop technical talent, hold technicians accountable, communicate confidently with clients and leadership, and step directly into complex technical situations when needed.

The TSM should be equally comfortable reviewing pod performance, coaching a technician, leading a client escalation, troubleshooting a complex technical issue, and partnering with Security or Compliance on a control-related concern.

In a CMMC environment, how the work is performed matters as much as whether the issue is resolved. The TSM is responsible for creating a culture where security, documentation, process adherence, technical excellence, and exceptional client service are part of everyday service delivery.